Methyl chloroformate → 2-Methoxycarbonylamino-indan-2-carboxylic acid

Participants

Reaction Steps

To a solution of 2-Amino-indan-2-carboxylic acid (0.45 g, 1.63 mmol) in CH2Cl2 (16 mL) was added HCl (in dioxanes, 4 M, 0.41 mL, 1.63 mmol). The solution was stirred at room temperature for 2 h and concentrated to dryness. The crude oil was dissolved in THF (6.5 mL). Aqueous NaOH (6 M, 0.92 mL, 5.5 mmol) and Methyl Chloroformate (0.15 mL, 1.95 mmol) were added and the resulting slurry was stirred at room temperature for 18 h. The reaction was diluted with HCl (1N) and extracted with Et2O (3 times). The combined organic layers were extracted with NaOH (2N, 3 times). The aqueous layers were acidified with HCl (6 N) and extracted with Et2O (3 times). The combined organic layers were dried over MgSO4 and concentrated. The crude oil was diluted in hexanes and concentrated again to provide 2-Methoxycarbonylamino-indan-2-carboxylic acid (0.35 g, 92%). LCMS-ESI+: calc'd for C12H13NO4: 235.08 (M+); Found: 235.94 (M+H+).

Provenance & Evidence